Six years ago, I received an invitation to attend a retreat at Esalen in Big Sur, California. The gathering was orchestrated by Bo Shao, then a newfound friend whom I’ve grown to admire—a successful entrepreneur and venture capitalist.

The concept of attending a retreat had never crossed my mind, and I had no preconceived notions. All I knew was that Bo had undergone a significant personal journey and was organizing an assembly to share those lessons and introduce his mentors. It was a substantial financial commitment—for me, at least—but I trusted Bo, and I was curious.

Our week-long stay brimmed with practical insights. The wisdom on offer left a lasting impact on me. When we were sharing reflections on the final day, I admitted that the retreat had made me realize I wasn’t the husband, father, son, or friend I thought I was. Which is to say, I wasn't the person I aspired to be. And yet, here were the tools I needed to bridge this gap. Gratitude sat heavily in my chest. 

We largely assume who we are and how we’re faring. Stepping out of our comfort zones, however, and surrounding ourselves with wise mentors are necessities. Confronting the truth of our identities without these components is a longshot. 

The timing of the retreat was somehow perfect, and I came out of it doing the real work of enhancing my relationships with my family, especially my brother, parents, wife, and daughters.

Some of the teachers who will be joining us at the Stray Reflections retreat in April at Canyon Ranch in Woodside, California, were there, my friends. They have played a significant role in my life since then.

The late professor Clayton Christensen cautioned against a tendency to overinvest in one’s career and seek tangible accomplishments while neglecting other vital aspects of life. His ideas resonate with our industry compatriots who, driven by ambition and the demands of the market, overlook the crucial areas until it’s too late, namely the intimate and loving relationships with family, which are ultimately the most powerful sources of enduring happiness. 

I am determined not to fall into that trap.

“Excellence,” if you allow me the quotation marks, has been my constant pursuit in work and faith. As my children grow older, however, my attention has turned more squarely toward parenting. I aspire to be an excellent father, and I acknowledge that it requires a lot of work.

After eleven years of marriage, I’ll admit it’s not an easy journey. Witnessing friends facing divorce or unhappiness in their marriages has made me more resolute to cultivate a fulfilling marriage. It calls for continuous effort. 

And so I’m broadening my perspective on work. It’s not merely about how I earn a living; it extends to all aspects of my life that hold significance. Everything, in essence, is a form of work. This realization emphas ongoing learning and growth in every dimension.

When we’re successful in investing, are we done? Well, no. Midlife presents a crucial choice: settling into routines or expanding our horizons. After all these years, our community is now primed to take on the big stuff together.

On Monday, April 15, we will be joined by Diana Chapman to focus on conscious leadership. The first step involves identifying and reducing drama. And by drama I mean unnecessary energy expenditure, repetitive issues, dysfunctional relationships, stress, and negative emotions. Instead, choosing radical responsibility, curiosity, and emotional expression leads to increased energy, clarity, focus, and healthier relationships.

Let’s put it like this: are you ready to cut the BS and live authentically? Doing more and more of what you’re passionate about and less and less of what you do out of obligation? According to Diana, the first mark of conscious leaders is self-awareness and the ability to tell themselves the truth.

On Tuesday, April 16, our focus turns to parenting. A profound insight for me was the recognition that how our children turn out can have everything to do with how we turn out as parents. So what I am I doing to enhance my skills as a father? Consider Patty Wipfler to be your parenting coach—she has played that role for me over the past six years.

As our teacher, she emphas the innate goodness in people, particularly children, and the importance of allowing the natural process of emotional release. Responding to kids as they need to be responded to, instead of in a manner reflective of our own past conditioning, requires surrender to the wisdom of who they are, who they are yet to become, and what they can teach us about ourselves in the process.

When Wednesday, April 17, rolls around, our attention shifts to relationships. While careers, children, and friendships may flourish, the bond with a life partner—the one you grow up and grow old with—is paramount. 

Roughly half of all marriages fail, and of those marriages left standing, how many are really fulfilling? How many truly great relationships do you see around you? Not merely a relationship you can live with, but one that is truly alive.

Terry Real, the renowned family therapist, will guide us to create and sustain a truly great marriage. He emphas building relationships thoughtfully, requiring as they do healthy self-esteem and a good relationship with oneself. According to Terry, maturity comes when we tend to our inner child and don’t inflict them on our partners to care for.

On Thursday, April 18, we’ll center on communication, the bedrock of every relationship.

While we may not consider the way we talk as “violent,” our words cause hurt and pain. There is a better way to communicate, one that deepens intimacy and connection, and it begins with recognizing our own feelings and needs, emphasizing honest expression without criticism, understanding the impact of words, and learning to ask for what we want.

Our teacher, Danny Cohen, says, “Imagine walking around in the world with the sense that everybody is on your team and motivated to help you get what you need to live a wonderful life. And that you derive great joy from making life more wonderful for other people. Most people I know long for flow, connection, intimacy, resilience, and a collaborative, caring spirit in both personal and professional relationships. Fewer people I know actually have grown up with the capacities and competencies that make these a real, everyday possibility.” 

I discovered non-violent communication six years ago, and ever since it has transformed the way I listen, communicate, and interact.

The practical wisdom on offer at the retreat I’ve invited you to is actionable and important. But that’s still only a part of it. 

Being in the same room, or in the same forest, with a collection of thirty people striving to become better humans and investors will make you wonder why you don’t do this more often. Built into our gathering is the space and time—in unusually nice surroundings—to allow for the weaving of social bonds and intellectual threads. The powerful connections you’ll make and the support system you’ll gain are invaluable, and you’ll watch them extend beyond the duration of the retreat.

We’ll gather in a luxury resort that is just half an hour from San Francisco International Airport. Canyon Ranch, surrounded by towering redwoods, is the sort of place where transformation happens. And we have it all to ourselves.

I understand that time and cost are significant considerations here. I want to assure you that we’ve thrown our heart into this rare and carefully curated few days, and the knowledge, skills, and experiences you’ll gain will make the time commitment worthwhile. The retreat is designed to be efficient and impactful, condensing a lot into relatively little time.

I encourage you to prioritize your well-being and consider the long-term impact that this retreat can have. Should questions linger, please reach out to me. This may be the most meaningful thing I’ve ever done, and I want to make it as feasible as possible for everyone committed to personal growth. 

I look forward to welcoming you to Woodside, California, next April for a week filled with practical wisdom, powerful connections, and life-changing tools. Together, let’s embark on a journey of self-discovery and growth and relief.